Potassium Carbonate → Phthalimide

Temperature

60 °C

A mixture of 7-methoxy-2-(R,S)-methylamino-1,2,3,4-tetrahydronaphthalene (3.02 g, 15.9 mmol), N-(4-bromobutyl)phthalimide (4.82 g, 17.1 mmol), anhydrous potassium carbonate (4.80 g, 34.7 mmol) and dry dimethylformamide (75 ml) was heated at 60° C. for 2 h, then left at room temperature for 18 h. Excess solvent was evaporated in vacuo, and the residue was partitioned between water (200 ml) and dichloromethane (3×100 ml). The organic phase was dried (Na2SO4) then evaporated in vacuo to give an oil. Chromatography on silica with 0-5% methanol-dichloromethane elution gave the intermediate phthalimide (3.8 g) as an oil which solidified. The latter was dissolved in ethanol (20 ml) and treated with hydrazine hydrate (2 ml; excess). Stirring at room temperature was carried out for 18 h, followed by reflux for 1 h. The mixture was cooled to 0° C., then filtered. The filtrate was evaporated in vacuo and the residue dissolved in dichloromethane (50 ml). Anhydrous sodium sulfate was added, and the mixture was filtered through kieselguhr. The filtrate was evaporated in vacuo to give the title compound (1.90 g, 46%).

1. customExcess solvent was evaporated in vacuo
2. customthe residue was partitioned between water (200 ml) and dichloromethane (3×100 ml)
3. dry with materialThe organic phase was dried (Na2SO4)
4. customthen evaporated in vacuo
5. customto give an oil
6. washChromatography on silica with 0-5% methanol-dichloromethane elution

ORD record

ord-99d8c87e9c4c4da6b6eede0169cc9f38

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06008219